Sulfamates of various structures, including those derived from monosaccharides, are described in J. Med. Chem. 1987, 30, 880 and in U.S. Pat. No. 4,075,351. Certain of these sulfamates are useful as pharmaceutical agents. More recently, sulfamates having various pharmaceutical activity in the areas of epilepsy, glaucoma, peptic ulcers, and male infertility are described in U.S. Pat. Nos. 4,513,006, 4,459,601 and 4,792,569. One of the compounds covered by U.S. Pat. No. 4,513,006, topiramate, has not only been found to exhibit particularly significant anticonvulsant activity in animals, but also appears to be useful in humans for the treatment of epilepsy (Drugs Future 1989, 14, 342).
While sulfamate compounds of the type disclosed in U.S. Pat. No. 4,513,006 have been shown to exhibit useful biological activity when administered to mammals, other compounds with equal or improved activity compared to topiramate would be desirable.
Replacement of the ring oxygen of cyclic monosaccharides by a methylene group affords an interesting class of compounds which has been referred to as "pseudo-sugars". These cyclotol compounds possess enhanced biological activity compared to the original monosaccharides.
Accordingly, it is an object of the present invention to describe novel pseudo-.beta.-fructopyranose sulfamate derivatives, which are related to topiramate, with potent anticonvulsant activity.